Windsor Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Joel Holland
Choose two or more items and save on your trip:
    Plan, book, travel with confidence
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    Better together
    Save up to NZ$545 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy
    Plan, book, and manage your trip all in one place

Our pick of the best Windsor Hotel Deals

Days Inn by Wyndham Madison NE/Windsor
Days Inn by Wyndham Madison NE/Windsor
2 out of 5
6311 Rostad Dr, I-90/94 and Hwy 19, Windsor, WI
Fully refundableReserve now, pay when you stay
The price is NZ$121 per night from 5 Jun to 6 Jun
NZ$121
per night
5 Jun - 6 Jun
7/10 Good! (762 reviews)
"Great Stay!"

Reviewed on 20 May 2024

Days Inn by Wyndham Madison NE/Windsor
The Madison Concourse Hotel and Governor's Club
The Madison Concourse Hotel and Governor's Club
3.5 out of 5
1 W Dayton St, Madison, WI
Fully refundableReserve now, pay when you stay
The price is NZ$259 per night from 16 Jun to 17 Jun
NZ$259
per night
16 Jun - 17 Jun
9.2/10 Wonderful! (1,649 reviews)
"The menu options in The Bar/Circ were very limited if gluten free"

Reviewed on 1 Jun. 2024

The Madison Concourse Hotel and Governor's Club
Best Western Plus InnTowner Madison
Best Western Plus InnTowner Madison
3 out of 5
2424 University Avenue, Madison, WI
Fully refundableReserve now, pay when you stay
The price is NZ$285 per night from 9 Jun to 10 Jun
NZ$285
per night
9 Jun - 10 Jun
9/10 Wonderful! (1,004 reviews)
"Great location very close to university. Parking on site. Good breakfast."

Reviewed on 31 May 2024

Best Western Plus InnTowner Madison
See all 387 properties in Windsor
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much does a Windsor holiday package cost?
From just . Yes, you read that right. Our Windsor packages are a simple way to make your dollar go further. Bundle your flights, hotels and rental car and explore this lively destination.
How do I get a cheap travel package to Windsor?
Booking a hotel and flight together with Expedia won’t just save you time — it’ll save you dollars too. A Windsor holiday package makes it easy to create your ideal trip. With more than 550 airlines across the world to pick from, finding flights that suit your schedule won’t be a problem. Not only that, we have over 1 000 000 hotel options globally to take your pick of. Now that’s choice! Whatever your budget, Expedia brings the world within your reach.
Where should I stay in Windsor?
There’s loads to do in Windsor, so spend your evenings close to its best sights and treat yourself to more time sightseeing. Mousehouse Cheesehaus is one spot to put on your itinerary.
What are the top hotels in Windsor?
Super 8 by Wyndham Windsor/Madison North and Days Inn by Wyndham Madison NE/Windsor are two of the most well-known properties in Windsor. Why not check out the rates and amenities at each and then make up your mind?
How far in advance should I book my Windsor holiday?
While not all air carriers advertise ticket prices early, customers are usually able to compare international fares on Expedia up to 12 months in advance. This is the time when you can score some incredible deals. If you’ve left things to the last minute, you might still be in luck. Low prices occasionally become available a few weeks before departure.
What does an Expedia Windsor travel package include?
Flights, car rentals and hotels — we bring you all the best deals. All you have to do is figure out your favourite combination. Once you’ve made your booking, you can add on the fun stuff like tours and experiences. Our travel packages make it simple to put together an exciting Windsor holiday.
What should I know before booking a Windsor travel package?
Find deals to match your budget with an Expedia package. Flights, hotels, rental cars — we’ve got them all. You’ll save precious cash just for bundling your bookings. Whether you’re embarking on a ski trip or drinking cocktails on a beach, your perfect getaway is just a few clicks away.
Can I choose my airline with a Windsor Expedia holiday package?
Yes, you’re in control. We have access to over 550 partner airlines around the world, so you can design your Windsor holiday according to your travel needs.
If I'm not able to travel, can I cancel my Windsor holiday package?
Certainly, and we’re here to help. You may be able to cancel and rebook your Windsor holiday package for free if you booked in the last 24 hours. However, you may be charged a fee by your hotel, airline or car rental company if you booked more than 24 hours ago. If your travel plans unexpectedly change, visit our Customer Service Portal for further information.

Discover the most popular places to visit in Windsor

Image for University of Wisconsin-Madison

University of Wisconsin-Madison

4/5(1 review)

Enjoy the student vibe around University of Wisconsin-Madison, a top university in Madison. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

University of Wisconsin-Madison
Image for Monona Terrace Community and Convention Center

Monona Terrace Community and Convention Center

4/5(1 review)

Learn about the events happening in Monona Terrace Community and Convention Center during your trip to Madison. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Monona Terrace Community and Convention Center
Image for Capitol Square

Capitol Square

4/5(1 review)

You can find out about the history of Madison when you stop by Capitol Square. Visit the area's shops or simply enjoy its restaurants.

Capitol Square

What to do in Windsor

Image for Madison Ghosts

Madison Ghosts

NZ$39
Per adult
Madison Ghosts
See all activities in Windsor
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.